OFF MARKET

Off Market Jun 2021 for $393K

$596,827

•

2,336

sq ft

21 Winding Way, Harpswell, ME 04079

About this home

Enjoy this peaceful and spacious home located on a private road in beautiful Harpswell Maine on nearly 2 acres. You will love the layout with over 2,300s. f of living space on three floors. The welcoming entrance takes you to an oversized dining room with pretty hardwood floors leading to the updated, spacious kitchen with white cabinets and huge pantry. The sunny living room features a wood stove, hardwood floors and convenient access to the wrap around deck. A first floor bedroom can easily double as a den or guest room. The oversized upstairs bedrooms are airy and bright with skylights and wood floors. Enjoy the bonus space downstairs with two more finished rooms, bathroom plus walk-out directly to the backyard. Beautiful perennial gardens and landscaping featuring rock walls, stairways and storage shed are situated on the 1.8 acre lot with over 400' of road frontage. You'll find walking trails, water access and beaches only a short drive away. In addition to being known for its beautiful coast, Harpswell also has amazingly low property taxes. A short 10 minute drive to Brunswick shopping and restaurants.

Single-familyProperty Type

1984Year Built

1.8 acresLot Size

$255Est. Price/Sq.Ft.

3 spacesParking

Listed by Timothy {Tim} Dunham • Tim Dunham Realty

Contact: 207-729-7297

Bought with Laura Byther • EXP Realty

Redfin checked: 2 minutes ago

•Source:MREIS #1487519

Redfin Estimate

$596,827

$204K since sold in June 2021$4,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 42.4% lower than the average sale price ($1.04M) of 6 comparable homes.

SOLD SEP 9, 2026
$1,250,000
A
3 beds2.5 baths2,524 sq ft
96 Shoal Cove Rd, West Bath, ME 04530
SOLD NOV 7, 2025
$629,000
B
3 beds2 baths2,269 sq ft
146 Oak Ledge Rd, Harpswell, ME 04079
SOLD JUN 24, 2026
$1,545,000
C
3 beds2 baths2,807 sq ft
42 Indian Point Ter, Harpswell, ME 04079
SOLD APR 17, 2026
$925,000
D
3 beds2 baths2,256 sq ft
4 Osprey Ridge Rd, Harpswell, ME 04079
SOLD JUL 1, 2026
$869,000
E
3 beds2 baths2,268 sq ft
132 Harpswell Neck Rd, Harpswell, ME 04079
SOLD JUL 9, 2026
$1,000,000
F
3 beds2.5 baths2,484 sq ft
42 Ridgeview Ln, Harpswell, ME 04079

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Earn from this home

Sell

$277,484

Est. take-home

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Rent

$2,786/mo

Redfin rental estimate

List your home for rent

Market trends in 04079, ME

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.7%

0.0% MoM

Median sale price

$850K

$368 MoM

Avg. days on market

14d

1 days MoM

Recently sold homes

4 MoM

New listings for sale

3D WALKTHROUGH
$1,295,000
3 beds2 baths1,890 sq ft
64 High Head Rd, Harpswell, ME 04079
OPEN TODAY, 11AM TO 4PM
$799,995
2 beds1.5 baths1,138 sq ft
7 Lower Rich Cove Rd, Harpswell, ME 04079
$8,500,000
7 beds6.5 baths6,753 sq ft
117 Starboard Ln, Harpswell, ME 04079
See all

Provided by Redfin

Sale history for 21 Winding Way

Date

Event

Price

MREIS #1487519

Jun 25, 2021

Sold

$393,000

$168/sq ft

May 1, 2021

Price Changed

$369,900

$158/sq ft

Apr 14, 2021

Listed

$391,000

$167/sq ft

MREIS #1414809

Jul 31, 2019

Sold

$282,000

$121/sq ft

May 16, 2019

Listed

$285,000

$122/sq ft

+33

Enjoy the peace and quiet of this private, year-round home in one of Maine's most desirable and picturesque coastal communities. Situated on a private road, this home boasts beautiful perennial gardens and landscaping featuring rock walls, stairways and even a horseshoe pit. Indoors, you'll find beautiful hardwood floors throughout, and a bonus space in the basement which makes for a perfect game room, den or private space when guests come to visit. Skylights in the upstairs bedrooms make the large rooms feel airy and bright. A wrap-around deck is the perfect spot to sit and watch the birds come and go. Large storage shed was once used as a horse stable and with a little TLC would once again be the perfect spot for some livestock. With walking trails, water access and beaches only a short drive away, this home is the perfect spot to get away from it all and enjoy nature and the beautiful coast.

Year

Property tax

Land + Additions

Assessment*

2025

$2,868 (+4.7%)

$80,700 + $350,000

$430,700

2024

$2,739 (+4.3%)

$80,700 + $350,000

$430,700

2023

$2,627 (+3.4%)

$80,700 + $350,000

$430,700

2022

$2,541 (−2.0%)

$80,700 + $350,000

$430,700

2021

$2,594 (+62.7%)

$76,500 + $307,300

$383,800

2020

$1,594 (+0.6%)

$76,500 + $160,000

$236,500

2019

$1,585 (+3.4%)

$76,500 + $160,000

$236,500

2018

$1,533 (+0.3%)

$76,500 + $160,000

$236,500

2017

$1,528 (+0.9%)

$76,500 + $160,000

$236,500

2016

$1,514 (+2.6%)

$76,500 + $160,000

$236,500

2015

$1,476

$76,500 + $160,000

$236,500

Tax history for 21 Winding Way

Year

Property tax

Land + Additions

Assessment*

2025

$2,868 (+4.7%)

$80,700 + $350,000

$430,700

2024

$2,739 (+4.3%)

$80,700 + $350,000

$430,700

2023

$2,627 (+3.4%)

$80,700 + $350,000

$430,700

2022

$2,541 (−2.0%)

$80,700 + $350,000

$430,700

2021

$2,594 (+62.7%)

$76,500 + $307,300

$383,800

2020

$1,594 (+0.6%)

$76,500 + $160,000

$236,500

2019

$1,585 (+3.4%)

$76,500 + $160,000

$236,500

2018

$1,533 (+0.3%)

$76,500 + $160,000

$236,500

2017

$1,528 (+0.9%)

$76,500 + $160,000

$236,500

2016

$1,514 (+2.6%)

$76,500 + $160,000

$236,500

2015

$1,476

$76,500 + $160,000

$236,500

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

78,408

Year renovated

—

Sq. Ft.

2,336

Year built

1984

Style

Single Family Residential

County

Cumberland County

APN

149783

Parking Spaces

Basement

Yes

Accessible

Yes

HOA Dues

$50 /month

Garage

Features

Green

Last updated by owner on May 29, 2026.

Property details

Parking

Parking Information
Parking Features: 1 - 4 Spaces, Gravel, On Site, Off Street

Interior

Virtual Tour

Bathroom Information
# of Baths (Full): 2

Room 1 Information
Type: Dining Room
Level: First
Features: Dining Area, Formal

Room 2 Information
Type: Kitchen
Level: First
Features: Eat-In Kitchen, Pantry

Room 3 Information
Type: Living Room
Level: First
Features: Heat Stove

Room 4 Information
Type: Bedroom 2
Level: Second
Features: Closet, Skylight

Room 5 Information
Type: Bedroom 3
Level: First
Features: Balcony/Deck

Room 6 Information
Type: Bedroom 4
Level: Basement
Features: Closet

Room 7 Information
Type: Primary Bedroom
Level: Second
Features: Closet, Full Bath, Skylight, Walk-In Closet(s)

Room 8 Information
Type: Bonus Room
Level: Basement

Basement Information
Basement Entry: Interior, Walk-Out Access, Daylight, Finished, Full

Interior Features
# of Rooms: 8
Interior Features: Walk-in Closets, 1st Floor Bedroom, Bathtub, Pantry, Shower, Primary Bedroom w/Bath
Washer, Refrigerator, Microwave, Electric Range, Dryer, Dishwasher
Window Features: Double-Pane Windows
Flooring: Wood, Vinyl, Tile, Laminate
Other Equipment: Internet Access Available, Generator, Cable

Exterior

Building Information
Construction Materials: Wood Siding, Vertical Siding, Wood Frame
Foundation Details: Concrete Perimeter
Roof: Metal, Pitched
Total Building Area (Sq. Ft.): 2,336
Building Area Source: Public Records

Exterior Features
Patio & Porch Features: Deck
Other Structures: Shed(s)

Property Information
Property Sub Type: Single Family Residence
Year Built: 1984
Above-Grade Finished Area (Sq. Ft.): 1,736
Below-Grade Finished Area (Sq. Ft.): 600

Lot Information
Lot Size (Sq. Ft.): $78,408
Lot Size (Acres): 1.8
Lot Size Source: Public Records
Lot Features: Well Landscaped, Rolling/Sloping, Wooded, Interior Lot, Rural
Road Surface Type: Gravel, Dirt
Zoning: INT

Subdivision Information
Subdivision Name: Winding Way Road Association

Financial

Tax Information
Annual Tax Amount: $1,594
Tax Year: 2020

Utilities

Utility Information
Has Heating
Heating: Zoned, Hot Water, Baseboard
Electric: Generator Hookup, Circuit Breakers
Sewer: Septic Tank, Private Sewer, Septic Design Available
Utilities: Utilities On
Utilities On: Yes
Water Source: Well, Private
Water Heater: Off Heating System, Oil, Tank

Location

HOA Information
Has Association
Association Fee: $285
Association Fee Frequency: Annually

Location Information
Unparsed Address: 21 Winding Way, Harpswell, ME 04079
Directions: From Cook's Corner, Take Route 24 towards Harpswell. Turn Left onto Cundy's Harbor Rd. Turn Left onto Grover St. Right onto Winding Way. House is the second on the left.

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 2,336
Stories: 2.0
Parking Spaces: 3
Basement: Yes
Accessible: Yes
Lot Size: 1.8 acres
Style: Single Family Residential
Year Built: 1984
Year Renovated: —
County: Cumberland County
APN: 149783
HOA Dues: $50/month
Garage: No
Features: Green

Home facts updated by owner on May 29, 2026

Around this home

Schools

Harpswell Community School

Public K-5 • Assigned • 1.5mi

9/10

Mt Ararat Middle School

Public 6-8 • Assigned • 9.4mi

6/10

Mt Ararat High School

Public 9-12 • Assigned • 8.9mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 85° expected this year, 18 days in 30 years

6/10 Wind Factor

64% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Harpswell, ME • 04079

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.3 hours in June and 4 hours in December, placing it below the U.S. average for solar exposure.

8.3 hrs

4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$567,000 – $687,000

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3D WALKTHROUGH

$1,295,000

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New listings for sale in 04079

3D WALKTHROUGH

$1,295,000

3 beds2 baths1,890 sq ft

64 High Head Rd, Harpswell, ME 04079

OPEN TODAY, 11AM TO 4PM

$799,995

2 beds1.5 baths1,138 sq ft

7 Lower Rich Cove Rd, Harpswell, ME 04079

$8,500,000

7 beds6.5 baths6,753 sq ft

117 Starboard Ln, Harpswell, ME 04079

Home values near 21 Winding Way

Data from public records.

Address	Redfin Estimate
77 Winding Way, Harpswell, ME 4 Beds \| 3 Baths \| 2087 Sq. Ft.	$1,184,102
66 Winding Way, Harpswell, ME 3 Beds \| 2 Baths \| 2122 Sq. Ft.	$672,412

Address	Redfin Estimate
131 Winding Way, Harpswell, ME 2 Beds \| 1.5 Baths \| 1025 Sq. Ft.	$1,404,834
16 Winding Way, Harpswell, ME 2 Beds \| 1 Baths \| 1344 Sq. Ft.	$479,432

Address	Redfin Estimate
34 Winding Way, Harpswell, ME 2 Beds \| 1.5 Baths \| 1536 Sq. Ft.	$509,461
81 Grover Lane, Harpswell, ME 2 Beds \| 1 Baths \| 1448 Sq. Ft.	$288,821

Property information provided by MREIS when last listed in 2021. This data may not show owner updates. Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 04079, ME

Sale history for 21 Winding Way

Tax history for 21 Winding Way

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 04079

Home values near 21 Winding Way

More real estate resources